5-Hydroxy-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone (AO 2210)
(±)-5-hydroxyl-1-(4′-hydroxyphenyl)-7-phenyl-3-heptanone have digestibility inhibition in vitro in cow rumen fluid.
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Journal of Chemical Ecology, 1999, 25(12):2703-2713.
Synthesis and Digestibility Inhibition of Diarylheptanoids: Structure–Activity Relationship.[Reference:
WebLink]
METHODS AND RESULTS:
(±)-5-Hydroxy-1,7-bis-(4′-hydroxyphenyl)-3-heptanone (2a), (±)-5-hydroxyl-1-(4′-hydroxyphenyl)-7-phenyl-3-heptanone (2b, 5-Hydroxy-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone (AO 2210)), (±)-5-hydroxy-7-(4′-hydroxyphenyl)-1-phenyl-3-heptanone (2c), and (±)-5-hydroxy-1,7-bis-(phenyl)-3-heptanone (2d) have been synthesized to study the structure–activity relationship regarding digestibility inhibition in vitro in cow rumen fluid. The activities were compared with the activity of chiral (S)-2a and its glucoside platyphylloside (1), isolated from Betula pendula.
CONCLUSIONS:
Compound 2a was slightly less active, 2b and 2c were more active, and 2d was less active than (S)-2a and platyphylloside.
